Past Winners Cup Competition
| Season | Winning Team |
| 2009/10 | Dunfermline Athletic |
| 2008/09 | Ross County |
| 2007/08 | Clyde |
| 2006/07 | St. Johnstone |
| 2005/06 | St. Mirren |
| 2004/05 | Gretna |
| 2003/04 | St. Johnstone |
| 2002/03 | St. Johnstone |
| 2001/02 | Arbroath |
| 2000/01 | Livingston |
| 1999/00 | Dunfermline Athletic |
| 1998/99 | Livingston |
| 1997/98 | Rangers |
| 1996/97 | Aberdeen |
| 1995/96 | Celtic |
| 1994/95 | Celtic |
| 1993/94 | Celtic |
| 1992/93 | Rangers |
| 1991/92 | Celtic |
| 1990/91 | Dundee United |
| 1989/90 | Celtic |
| 1988/89 | Heart of Midlothian |
| 1987/88 | Motherwell |
| 1986/87 | Dundee |
| 1985/86 | Celtic |
| 1984/85 | Aberdeen |
| 1983/84 | Hamilton Academical |
| 1982/83 | Dundee United |
| 1981/82 | Ayr United |
| 1980/81 | Celtic |
| 1979/80 | Celtic |
| 1978/79 | Aberdeen |
| 1977/78 | St. Mirren |
| 1976/77 | Rangers |
| 1975/76 | Rangers |
| 1974/75 | Rangers |
| 1973/74 | Partick Thistle |
| 1972/73 | Aberdeen |
| 1971/72 | Heart of Midlothian |
| 1970/71 | Celtic |
| 1969/70 | Celtic |
| 1968/69 | Celtic |
| 1967/68 | Rangers |
| 1966/67 | Celtic |
| 1965/66 | Hibernian |
| 1964/65 | Kilmarnock |
| 1963/64 | Dundee United |
| 1962/63 | Rangers |
| 1961/62 | Rangers |
| 1960/61 | Rangers |
| 1959/60 | Celtic |
| 1958/59 | Falkirk |
| 1957/58 | Aberdeen |
| 1956/57 | Aberdeen |
| 1955/56 | Falkirk |
| 1954/55 | No Competition |
| 1953/54 | No Competition |
| 1952/53 | No Competition |
| 1951/52 | No Competition |
| 1950/51 | No Competition |
| 1949/50 | No Competition |
| 1948/49 | Hibernian |
| 1947/48 | Hibernian |
| 1946/47 | Hibernian |